Trimethylsilyl azide

Trimethylsilyl azide

Names
IUPAC name Azido(trimethyl)silane
Identifiers
CAS Number	4648-54-8 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1903730
ChemSpider	70747 Y
ECHA InfoCard	100.022.798
EC Number	225-078-5
PubChem CID	78378
InChI InChI=1S/C3H9N3Si/c1-7(2,3)6-5-4/h1-3H3 Y Key: SEDZOYHHAIAQIW-UHFFFAOYSA-N Y InChI=1/C3H9N3Si/c1-7(2,3)6-5-4/h1-3H3 Key: SEDZOYHHAIAQIW-UHFFFAOYAJ
SMILES [N-]=[N+]=N[Si](C)(C)C
Properties
Chemical formula	C3H9N3Si
Molar mass	115.21 g·mol−1
Appearance	clear liquid, colorless
Density	0.8763 g/cm3 (20 °C)
Melting point	−95 °C (−139 °F; 178 K)
Boiling point	52 to 53 °C (126 to 127 °F; 325 to 326 K) at 175 mmHg (92 to 95 °C at 760 mmHg)
Solubility in water	reacts to form dangerous hydrazoic acid
Hazards
R-phrases (outdated)	R11, R23, R24, R25, R29, R50, R51, R52, R53
S-phrases (outdated)	S16,S29,S36, S37,S45,S57,S8,
NFPA 704	3 4 0
Flash point	6 °C (43 °F; 279 K)
Autoignition temperature	> 300 °C (572 °F; 573 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Trimethylsilyl azide ((CH₃)₃SiN₃) is a chemical compound used as a reagent in organic chemistry.

Trimethylsilyl azide is commercially available. It may be prepared by the reaction of trimethylsilyl chloride and sodium azide:

It is considered a safer replacement for hydrazoic acid in many reactions. It will however over time hydrolyze to hydrazoic acid and therefore it must be stored free of moisture It has been used in the Oseltamivir total synthesis.

Trimethylsilyl azide is incompatible with moisture, strong oxidizing agents, and strong acids. In 2014, a graduate student at the University of Minnesota was injured in an explosion that occurred in the synthesis of a large batch of trimethylsilyl azide.